WO2021015172A1 - Composition de composé hydrocarbure aliphatique saturé ainsi que procédé de fabrication de celle-ci, et composition d'huile lubrifiante - Google Patents

Composition de composé hydrocarbure aliphatique saturé ainsi que procédé de fabrication de celle-ci, et composition d'huile lubrifiante Download PDF

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WO2021015172A1
WO2021015172A1 PCT/JP2020/028118 JP2020028118W WO2021015172A1 WO 2021015172 A1 WO2021015172 A1 WO 2021015172A1 JP 2020028118 W JP2020028118 W JP 2020028118W WO 2021015172 A1 WO2021015172 A1 WO 2021015172A1
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Prior art keywords
aliphatic hydrocarbon
saturated aliphatic
hydrocarbon compound
compound composition
olefin
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PCT/JP2020/028118
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English (en)
Japanese (ja)
Inventor
横田　清彦
清和 片山
佳奈子 鮫島
各務　成存
幸太 大場
直幸 植田
貴浩 阪口
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出光興産株式会社
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Application filed by 出光興産株式会社 filed Critical 出光興産株式会社
Priority to MX2022000890A priority Critical patent/MX2022000890A/es
Priority to CN202080052938.1A priority patent/CN114127238B/zh
Priority to JP2021534030A priority patent/JP7525491B2/ja
Priority to EP20844170.9A priority patent/EP4006126A4/fr
Priority to CA3148235A priority patent/CA3148235A1/fr
Priority to KR1020227005498A priority patent/KR20220042152A/ko
Priority to US17/629,173 priority patent/US20220251461A1/en
Publication of WO2021015172A1 publication Critical patent/WO2021015172A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
    • C10G69/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only
    • C10G69/12—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step
    • C10G69/126—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step polymerisation, e.g. oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
    • C07C2/08—Catalytic processes
    • C07C2/26—Catalytic processes with hydrides or organic compounds
    • C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
    • C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
    • C07C5/25—Migration of carbon-to-carbon double bonds
    • C07C5/2506—Catalytic processes
    • C07C5/2562—Catalytic processes with hydrides or organic compounds
    • C07C5/2575—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/04—Purification; Separation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/58—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins
    • C10G45/60—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins characterised by the catalyst used
    • C—CHEMISTRY; METALLURGY
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    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
    • C10G50/02—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation of hydrocarbon oils for lubricating purposes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02—Well-defined hydrocarbons
    • C10M105/04—Well-defined hydrocarbons aliphatic
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C10M107/10—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing aliphatic monomer having more than 4 carbon atoms
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/02—Specified values of viscosity or viscosity index
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1062—Lubricating oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1088—Olefins
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/30—Physical properties of feedstocks or products
    • C10G2300/302—Viscosity
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/30—Physical properties of feedstocks or products
    • C10G2300/304—Pour point, cloud point, cold flow properties
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    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/10—Lubricating oil
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/0206—Well-defined aliphatic compounds used as base material
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/022—Well-defined aliphatic compounds saturated
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/011—Cloud point
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
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    • C10N2020/02—Viscosity; Viscosity index
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/72—Extended drain
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/74—Noack Volatility
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    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/02—Reduction, e.g. hydrogenation
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    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • the present invention relates to a saturated aliphatic hydrocarbon compound composition, a lubricating oil composition, and a method for producing a saturated aliphatic hydrocarbon compound composition.
  • lubricating oils are required to have long drainage properties from the viewpoint of resource saving in addition to environmental protection. In order to improve the long drainage property, stability against heat and oxidation reaction is required.
  • Various synthetic lubricating oils have been developed as such lubricating oils having excellent stability.
  • poly ⁇ -olefin, polybutene, alkylbenzene, polyol ester, dibasic acid ester, polyoxyalkylene glycol, polyoxyalkylene glycol ester, polyoxyalkylene glycol ether, silicone and the like are used as base oils for synthetic lubricating oils. ..
  • poly- ⁇ -olefins having high chemical stability and excellent viscosity index are widely used.
  • poly- ⁇ -olefin having the desired viscosity is widely used. Oolefins are manufactured and used. Under these circumstances, attempts have been made to efficiently obtain poly ⁇ -olefins having a controlled structure.
  • Patent Document 1 ⁇ -olefin is dimerized in the presence of a Cheegler catalyst, and the obtained dimer is further dimerized in the presence of a Friedel-Crafts catalyst or an acid catalyst and hydrogenated. , 11,13-Dioctyl-13-Methyltricosane, and other methods of obtaining specific saturated aliphatic hydrocarbons have been disclosed.
  • Patent Document 2 describes that as a method for obtaining a component of a lubricating oil composition having excellent oxidative stability, thermal stability and low temperature stability, a vinylidene olefin is produced by dimerizing ⁇ -olefin in the presence of a metallocene complex catalyst.
  • a method for producing a saturated aliphatic hydrocarbon compound in which the vinylidene olefin is further dimerized in the presence of an acid catalyst and the obtained dimerized product is hydrogenated.
  • Patent Document 3 in order to obtain a low-viscosity oil containing 9-methyl-11,13-dioctilty lycosane, 1-decene is oligomerized in the presence of hydrogen, a metallocene catalyst and an activator compound to obtain hydrogen.
  • a method of catalytically hydrogenating an oligomerization product in the presence of a hydrogenation catalyst and separating the obtained tetramer distillate by vacuum distillation.
  • a low-viscosity base oil is required as a lubricating oil for machines. Therefore, the degree of polymerization and the like are adjusted as described above to obtain a poly- ⁇ -olefin having a low viscosity.
  • conventionally in order to lower the viscosity, it is necessary to lower the molecular weight, but when the molecular weight is lowered, it becomes easy to evaporate, and there is a problem that the long drainage property deteriorates. Therefore, in order to achieve both lubrication characteristics and long drainage properties, a poly ⁇ -olefin that serves as a base oil for a lubricating oil having a low viscosity and excellent evaporation resistance has been required.
  • An object of the present invention is to contain a saturated aliphatic hydrocarbon compound composition having a low viscosity and a small evaporation loss, which can be used as a base oil for a lubricating oil to obtain a lubricating oil having a long life.
  • the present invention provides a method for producing a lubricating oil composition and a saturated aliphatic hydrocarbon compound composition.
  • a saturated aliphatic hydrocarbon compound composition having a specific physical property and a specific average carbon number has a low viscosity, a small evaporation loss, and a lubricating oil.
  • a lubricating oil having a long life can be obtained when used as a base oil of the above, and have reached the present invention.
  • the present invention relates to the following (1) to (13).
  • composition (4) The saturation according to any one of (1) to (3), wherein the content of 11-methyl-11,13-dioctyl lycosane in the saturated aliphatic hydrocarbon compound having 40 carbon atoms is 40% by mass or less.
  • Aliphatic hydrocarbon compound composition (5) A lubricating oil composition containing the saturated aliphatic hydrocarbon compound composition according to any one of (1) to (4).
  • Production of a saturated aliphatic hydrocarbon compound composition comprising a step 1 of oligomerizing an olefin to obtain an olefin oligomer, a step 2 of isomerizing the olefin oligomer to obtain an isomer, and a step 3 of hydrogenating the isomer.
  • step 2 is isomerization in the presence of a Friedel-Crafts catalyst.
  • step 1 is an oligomerization in the presence of a Friedel-Crafts catalyst.
  • step 9 The method for producing a saturated aliphatic hydrocarbon compound composition according to (7) or (8), wherein the Friedel-Crafts catalyst contains organoaluminum.
  • step 10 The method for producing a saturated aliphatic hydrocarbon compound composition according to any one of (6) to (9), which comprises step 4 which is a distillation step after step 3.
  • a saturated aliphatic hydrocarbon compound composition having a low viscosity and a small evaporation loss which can be used as a base oil for a lubricating oil to obtain a lubricating oil having a long life, and the composition thereof are contained.
  • a method for producing a lubricating oil composition and a saturated aliphatic hydrocarbon compound composition can be provided.
  • the present invention is a saturated aliphatic hydrocarbon compound composition having a weight loss by evaporation of 4% by mass or less by the Noack method, a kinematic viscosity at 100 ° C. of 6.5 mm 2 / sec or less, and an average carbon number of 36 to 44.
  • This is a method for producing a saturated aliphatic hydrocarbon compound composition, which comprises step 3 of adding water.
  • the present invention will be described in detail below.
  • the saturated aliphatic hydrocarbon compound composition of the present invention has a weight loss by evaporation of 4% by mass or less by the Noack method, a kinematic viscosity of 6.5 mm 2 / sec or less at 100 ° C., and an average carbon number of 36 to 44. is there.
  • the saturated aliphatic hydrocarbon compound composition of the present invention has an average carbon number of 36 to 44, preferably 38 to 42, more preferably 39 to 42, and even more preferably 39 to 41.
  • the saturated aliphatic hydrocarbon compound composition of the present invention preferably contains a saturated aliphatic hydrocarbon compound having 40 carbon atoms as a component thereof, and preferably contains the most saturated aliphatic hydrocarbon compound having 40 carbon atoms. , It is more preferable to contain a saturated aliphatic hydrocarbon compound having 40 carbon atoms as a main component.
  • the content of the saturated aliphatic hydrocarbon compound having 40 carbon atoms is preferably 20% by mass or more, more preferably 30% by mass or more, still more preferably 50% by mass or more in the saturated aliphatic hydrocarbon compound composition. 90% by mass or more is further preferable, 92% by mass or more is further preferable, and 94% by mass or more is further preferable.
  • a lubricating oil having a low viscosity and a long life can be obtained when used as a base oil.
  • the area of the main peak is preferably 40% or less among the peaks corresponding to the saturated aliphatic hydrocarbon compound having 40 carbon atoms in the chromatogram by gas chromatography. 35% or less is more preferable, 30% or less is further preferable, 25% or less is further preferable, and 23% or less is further preferable.
  • the area of the peak in the chromatogram by gas chromatography can be determined by the method described in Examples, and the detector used here is a FID (hydrogen flame ionization detector).
  • the saturated aliphatic hydrocarbon compound composition of the present invention is mainly composed of a saturated aliphatic hydrocarbon compound having 40 carbon atoms, and the saturated aliphatic hydrocarbon compound having 40 carbon atoms contains a plurality of isomers. contains. Therefore, when the gas chromatography analysis of the saturated aliphatic hydrocarbon compound composition is performed, a plurality of peaks corresponding to the saturated aliphatic hydrocarbon compound having 40 carbon atoms are found. Among them, the peak having the largest area is defined as the main peak.
  • the compound corresponding to the main peak is not clear, but it is considered to be 11-methyl-11,13-dioctilt docusate. Therefore, the content of 11-methyl-11,13-dioctilt lycosane in the saturated aliphatic hydrocarbon compound having 40 carbon atoms in the saturated aliphatic hydrocarbon compound composition of the present invention is 40% by mass or less. Preferably, 35% by mass or less is more preferable, 30% by mass or less is further preferable, 25% by mass or less is further preferable, and 23% by mass or less is further preferable.
  • the saturated aliphatic hydrocarbon compound composition of the present invention has a low viscosity, a small evaporation loss, and a long life when used as a base oil is not clear, but it is considered as follows. .. Since 11-methyl-11,13-dioctilt lycosane has a quaternary carbon, it is considered that it is easily oxidatively decomposed by an external stimulus such as heat. However, the saturated aliphatic hydrocarbon compound composition of the present invention has It is considered that this is because there are few saturated aliphatic hydrocarbon compounds having quaternary carbons and isomers having a more stable structure are the main constituents.
  • the ratio of quaternary carbon per molecule to the carbon atoms of the saturated aliphatic hydrocarbon compound composition having an average carbon number of 36 to 44 in the present invention is preferably 1.0% or less, preferably 0.88%.
  • the following is more preferable, 0.75% or less is further preferable, 0.63% or less is further preferable, and 0.58% or less is further preferable.
  • the saturated aliphatic hydrocarbon compound composition of the present invention has excellent properties of low viscosity and little evaporation loss.
  • the weight loss by evaporation of the saturated aliphatic hydrocarbon compound composition of the present invention by the Noack method is 4% by mass or less, preferably 3.9% by mass or less, more preferably 3.8% by mass or less, and 3.6% by mass or less. The following is more preferable.
  • the smaller the evaporation weight loss by the Noack method the more preferably 0% by mass, but in the case of a saturated aliphatic hydrocarbon compound composition having an average carbon number of 36 to 44, it is usually 3.0% by mass or more. Is.
  • the kinematic viscosity of the saturated aliphatic hydrocarbon compound composition of the present invention at 100 ° C. is 6.5 mm 2 / sec or less, preferably 6.3 mm 2 / sec or less, more preferably 6.1 mm 2 / sec or less. More preferably, it is 6.0 mm 2 / sec or less.
  • the preferred kinematic viscosity at 100 ° C. varies depending on the application in which the lubricating oil is used, but is usually 5.0 mm 2 / sec or more for a saturated aliphatic hydrocarbon compound composition having an average carbon number of 36 to 44. ..
  • the saturated aliphatic hydrocarbon compound composition of the present invention is preferably 40 mm 2 / sec or less, more preferably less 35 mm 2 / sec, more preferably less 32 mm 2 / sec, 31 mm 2 / sec Is even more preferable.
  • the preferred kinematic viscosity at 40 ° C. varies depending on the application in which the lubricating oil is used, but is usually 25 mm 2 / sec or more for a saturated aliphatic hydrocarbon compound composition having an average carbon number of 36 to 44.
  • the viscosity index of the saturated aliphatic hydrocarbon compound composition of the present invention is preferably 110 or more, more preferably 120 or more, further preferably 130 or more, still more preferably 140 or more.
  • a suitable viscosity index varies depending on the application in which the lubricating oil is used, but is usually 150 or less for a saturated aliphatic hydrocarbon compound composition having an average carbon number of 36 to 44.
  • the low temperature cranking viscosity (CCS) of the saturated aliphatic hydrocarbon compound composition of the present invention is preferably 4000 mPa ⁇ s or less, more preferably 3700 mPa ⁇ s or less, further preferably 3500 mPa ⁇ s or less, and more preferably 3400 mPa ⁇ s or less. More preferred.
  • the suitable low temperature cranking viscosity (CCS) varies depending on the application in which the lubricating oil is used, but is usually 3000 Pa ⁇ s or more for a saturated aliphatic hydrocarbon compound composition having an average carbon number of 36 to 44.
  • the pour point of the saturated aliphatic hydrocarbon compound composition of the present invention is preferably ⁇ 40 ° C. or lower, more preferably ⁇ 50 ° C. or lower.
  • the method for producing a saturated aliphatic hydrocarbon compound composition of the present invention includes a step 1 of oligomerizing an olefin to obtain an olefin oligomer, a step 2 of isomerizing the olefin oligomer to obtain an isomer, and hydrogenation of the isomer. Step 3 is included.
  • the saturated aliphatic hydrocarbon compound composition obtained by this production method has the saturated aliphatic hydrocarbon compound composition, that is, the evaporation loss by the Noack method is 4% by mass or less, and the kinematic viscosity at 100 ° C. is 6.5 mm.
  • the saturated aliphatic hydrocarbon compound composition may be used. It is possible to efficiently manufacture products that are not included in the range of products.
  • the saturated aliphatic hydrocarbon compound composition obtained by this production method has extremely reduced evaporation by the Noack method as long as the kinematic viscosity is the same as that of the saturated aliphatic hydrocarbon compound composition obtained by other production methods.
  • the olefin used in the method for producing the saturated aliphatic hydrocarbon compound composition of the present invention is preferably vinylidene olefin, ⁇ -olefin, or a mixture thereof, and more preferably vinylidene olefin or a mixture of vinylidene olefin and ⁇ -olefin. Vinylidene olefins are more preferred.
  • the saturated aliphatic hydrocarbon compound composition having an average carbon number of 36 to 44 is obtained by the method for producing a saturated aliphatic hydrocarbon compound composition of the present invention, the olefin used in the present production method has 20 carbon atoms.
  • the content of the olefin is preferably 80% by mass or more, more preferably 85% by mass or more, further preferably 90% by mass or more, still more preferably 91% by mass or more.
  • the saturated aliphatic hydrocarbon compound composition having the average carbon number of 36 to 44 can be efficiently obtained.
  • the vinylidene olefin is preferably one or more selected from the compounds represented by the following general formula (1).
  • R 1 and R 2 each independently represent a hydrogen atom or an alkyl group having a linear or branched carbon number of 1 to 16).
  • R 1 and R 2 are each independently a hydrogen atom or an alkyl group having a linear or branched carbon number of 1 to 16, but in the present invention, they have 8 to 16 carbon atoms. It is preferably a linear alkyl group.
  • the linear alkyl group having 8 to 16 carbon atoms include n-octyl group, n-nonyl group, n-decyl group, n-undecylic group, n-dodecyl group, n-tridecyl group and n-tetradecyl group. Examples thereof include an n-pentadecyl group and an n-hexadecyl group.
  • the vinylidene olefin is preferably produced by dimerizing an ⁇ -olefin.
  • ⁇ -olefin those shown in the section ( ⁇ -olefin) described later can be preferably used, but among them, ⁇ -olefins having 6 to 12 carbon atoms are preferable, and ⁇ -olefins having 8 to 10 carbon atoms are preferable. Oolefins are more preferred.
  • a linear ⁇ -olefin is preferable, a linear ⁇ -olefin having 6 to 12 carbon atoms is more preferable, and a linear ⁇ -olefin having 8 to 10 carbon atoms is further preferable.
  • Specific examples of the ⁇ -olefin include 1-octene, 1-decene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene and the like.
  • ⁇ -Ocene, 1-decene, 1-dodecene and 1-tetradecene are preferable, 1-octene and 1-decene are more preferable, and 1-decene is more preferable.
  • These ⁇ -olefins may be used alone or in combination of two or more. That is, when the olefin used in this production method is a vinylidene olefin, the olefins used in this production method are 1-octene dimer, 1-decene dimer, 1-dodecene dimer, 1-.
  • a dimer of tetradecene is preferable, a dimer of 1-octene and a dimer of 1-decene are more preferable, and a dimer of 1-decene is more preferable.
  • vinylidene olefins can be selectively obtained in high yield by carrying out the reaction in the presence of a catalyst.
  • a catalyst used in the dimerization of ⁇ -olefin a metallocene catalyst is preferable.
  • the metallocene complex catalyst includes (i) a metallocene complex having a ligand having a conjugated five-membered carbon ring and containing a transition metal of Group 4 to 6 of the periodic table, and (ii) and (ii-1) cations. It is preferable to use a catalyst containing at least one selected from a compound consisting of an anions in which a plurality of groups are bonded to an element and an organoaluminum compound (ii-2).
  • the metallocene complex of Group 4 to 6 of the Periodic Table which has a ligand having a conjugated carbon five-membered ring of the component (i) constituting the catalyst, has the following general formula (2) in terms of activity as a catalyst.
  • the transition metal compound represented by the general formula (3) is preferable.
  • Q 1 indicates a binding group that crosslinks two conjugated five-membered ring ligands (C 5 H 5-ab R 3 b ) and (C 5 H 5-ac R 4 c ), and Q 2 Indicates a binding group that crosslinks a conjugated five-membered ring ligand (C 5 H 5-ad R 5 d ) with a Z group.
  • E + f is (valence of M 1-2 ).
  • M 1 represents a transition metal of Group 4 to 6 of the Periodic Table.
  • X, Y and Z represent covalent or ionic binding ligands, respectively.
  • Q 1 and Q 2 (1) methylene group, an ethylene group, isopropylene group, methylphenyl group, a diphenylmethylene group, an alkylene group having 1 to 4 carbon atoms such as cyclohexylene group, a cycloalkylene group Or its side chain lower alkyl or phenyl substituent, (2) silylene group such as silylene group, dimethyl silylene group, methylphenyl silylene group, diphenyl silylene group, disylylene group, tetramethyl disylylene group, oligosilylene group or its side chain Lower alkyl or phenyl substituent, (3) (CH 3 ) 2 Ge group, (C 6 H 5 ) 2 Ge group, (CH 3 ) P group, (C 6 H 5 ) P group, (C 4 H 9 ) N group, (C 6 H 5 ) N group, (CH 3 ) B group, (C 4 H 9 ) B group, (C 6 H 5 ) B group,
  • (C 5 H 5-ab R 3 b ), (C 5 H 5-ac R 4 c ) and (C 5 H 5-ad R 5 d ) are conjugated five-membered ring ligands, and R 3 , R 4 and R 5 represent hydrocarbon groups, halogen atoms, alkoxy groups, silicon-containing hydrocarbon groups, phosphorus-containing hydrocarbon groups, nitrogen-containing hydrocarbon groups or boron-containing hydrocarbon groups, respectively, where a is 0, 1 Or 2.
  • the hydrocarbon group preferably has 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
  • this hydrocarbon group may be bonded to a cyclopentadienyl group which is a conjugated five-membered ring group, and when a plurality of these groups are present, the two are bonded to each other and cyclo.
  • a ring structure may be formed together with a part of the pentadienyl group.
  • typical examples of the conjugated five-membered ring ligand are a substituted or unsubstituted cyclopentadienyl group, an indenyl group and a fluorenyl group.
  • the halogen atom include chlorine, bromine, iodine and fluorine atoms
  • examples of the alkoxy group include those having 1 to 12 carbon atoms.
  • Examples of the silicon-containing hydrocarbon group include ⁇ Si (R 6 ) (R 7 ) (R 8 ) (R 6 , R 7 and R 8 are hydrocarbon groups having 1 to 24 carbon atoms) and the like, and contain phosphorus.
  • Hydrocarbon groups, nitrogen-containing hydrocarbon groups and boron-containing hydrocarbon groups include -P (R 9 ) (R 10 ), -N (R 9 ) (R 10 ) and -B (R 9 ) (R 10 ), respectively. ) (R 9 and R 10 are hydrocarbon groups having 1 to 18 carbon atoms) and the like.
  • R 3 , R 4, and R 5 When there are a plurality of R 3 , R 4, and R 5 , the plurality of R 3 , the plurality of R 4, and the plurality of R 5 may be the same or different.
  • the conjugated five-membered ring ligands C 5 H 5-ab R 3 b ) and (C 5 H 5-ac R 4 c ) may be the same or different. ..
  • Examples of the hydrocarbon group having 1 to 24 carbon atoms or the hydrocarbon group having 1 to 18 carbon atoms include an alkyl group, an alkenyl group, an aryl group, an alicyclic aliphatic hydrocarbon group and the like.
  • Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-hexyl group, an n-decyl group and the like, and have 1 to 1 carbon atoms. 20 is preferable.
  • Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 1-butenyl group, a 1-hexenyl group, a 1-octenyl group, a cyclohexenyl group and the like, and those having 2 to 10 carbon atoms are preferable in the present invention.
  • Examples of the aryl group include a phenyl group, a tolyl group, a xsilyl group, a naphthyl group and the like, and those having 6 to 14 carbon atoms are preferable in the present invention.
  • Examples of the alicyclic aliphatic hydrocarbon group include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • M 1 represents a transition metal element of Group 4 to 6 of the Periodic Table, and specific examples thereof include titanium, zirconium, hafnium, vanadium, niobium, molybdenum, and tungsten. Among these, as a catalyst. Tungsten, zirconium and hafnium are preferable from the viewpoint of activity.
  • Z is a covalent ligand, a halogen atom, oxygen (-O-), sulfur (-S-), an alkoxy group having 1 to 20 carbon atoms (preferably 1 to 10), and 1 to 20 carbon atoms.
  • a thioalkoxy group (preferably 1 to 12), a nitrogen-containing hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 18) (for example, a t-butylamino group, a t-butylimino group, etc.), a carbon number of 1 to 1 to 18 It shows 40 (preferably 1-18) phosphorus-containing hydrocarbon groups.
  • X and Y are covalent or covalent ligands, respectively, and specifically, a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10), and the like.
  • 20 preferably 1-12) silicon-containing hydrocarbon groups (eg, trimethylsilyl group), 1-20 (preferably 1-12) carbon hydrocarbon groups or halogen-containing boron compounds (eg B (C) 6 H 5 ) 4 , BF 4 ) is shown. Of these, halogen atoms and hydrocarbon groups are preferred.
  • the X and Y may be the same as or different from each other.
  • a complex having a ligand having an indenyl, cyclopentadienyl or fluorenyl structure is particularly preferable.
  • Examples of the transition metal compound represented by the general formula (2) or (3) include (a) a transition metal compound having no bonding group to be crosslinked and having two conjugated five-membered ring ligands, and (b) alkylene.
  • a transition metal compound having two conjugated five-membered ring ligands cross-linked with a group (c) a transition metal compound having two conjugated five-membered ring ligands bridged with a silylene group, (d) germanium, aluminum, boron, phosphorus.
  • a transition metal compound having two conjugated five-membered ring ligands cross-linked with a hydrocarbon group containing nitrogen (e) a transition metal compound having one conjugated five-membered ring ligand, and (f) a ligand.
  • the chlorine atom of these compounds is bromine
  • examples thereof include those substituted with an atom, an iodine atom, a hydrogen atom, a methyl group, a phenyl group, a benzyl group, a methoxy group, a dimethylamino group, or the like.
  • Compounds are preferably used.
  • the compound composed of the (ii-1) cation among the (ii) components constituting the catalyst and the anion in which a plurality of groups are bonded to the element is not particularly limited, but the following formula (4) or The compound represented by (5) can be preferably used.
  • L 2 is M 4 , R 12 R 13 M 5 , R 14 3 C, R 15 R 16 R 17 R 18 N or R 19 R 20 R 21 S.
  • L 1 is a Lewis base
  • R 11 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylaryl group or an arylalkyl group
  • M 2 and M 3 are periodic tables, respectively.
  • Z 1 ⁇ Z n are each a hydrogen atom, a dialkylamino group, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms , alkylaryl group, arylalkyl group, halogen-substituted hydrocarbon group having 1 to 20 carbon atoms, an acyloxy group having 1 to 20 carbon atoms, an organic metalloid group or a halogen atom, Z 1 ⁇ Z n is 2 or more thereof together They may be combined to form a ring.
  • m is the valence of M 2 and M 3 and is an integer of 1 to 7
  • n is an integer of 2 to 8
  • k is the valence of [L 1- R 11 ] and [L 2 ] and is an integer of 1 to 7.
  • p is an integer of 1 or more
  • q (p ⁇ k) / (nm).
  • M 4 is an element selected from the 1st and 11th groups of the periodic table
  • M 5 is an element selected from the 8th, 9th and 10th groups of the periodic table
  • R 12 and R 13 are.
  • R 14 represents an alkyl group having 1 to 20 carbon atoms, an aryl group, an alkylaryl group or an arylalkyl group, respectively.
  • R 15 to R 21 represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylaryl group, an arylalkyl group, a substituted alkyl group or an organic metalloid group, respectively.
  • Lewis base (L 1 ) examples include ammonia, methylamine, aniline, dimethylamine, diethylamine, N-methylaniline, diphenylamine, trimethylamine, triethylamine, tri-n-butylamine, N, N-dimethylaniline, and methyl.
  • Amines such as diphenylamine, pyridine, p-promo-N, N-dimethylaniline, p-nitro-N, N-dimethylaniline, phosphines such as triethylphosphine, triphenylphosphine, diphenylphosphine, dimethyl ether, diethyl
  • phosphines such as triethylphosphine, triphenylphosphine, diphenylphosphine, dimethyl ether, diethyl
  • ethers such as ether, tetrahydrofuran and dioxane
  • thioethers such as diethyl thioether and tetrahydrothiophene
  • esters such as ethyl benzoate.
  • M 2 and M 3 include B, Al and the like
  • specific examples of M 4 include Na, Ag, Cu and the like
  • specific examples of M 5 include Fe, Co and the like.
  • those in which M 2 and M 3 are boron are preferable, and in particular, the compound in which M 2 is boron in the general formula (4) is preferable.
  • Examples of the (ii-2) organoaluminum compound among the (ii) components constituting the catalyst include compounds represented by the following general formulas (6), (7) or (8).
  • R 22 r AlQ 3 3-r (6) R 22 is an alkyl group having 1 to 20 carbon atoms (preferably 1 to 12), an alkenyl group, an aryl group, an arylalkyl group or other hydrocarbon group, Q 3 is a hydrogen atom, an alkoxy group having 1 to 20 carbon atoms or Represents a halogen atom.
  • R is a number from 1 to 3.
  • R 22 is the same as described above.
  • S represents the degree of polymerization and is usually 3 to 50.
  • R 22 is the same as described above, and s represents the degree of polymerization, preferably 3 to 50.
  • Cyclic alkylaluminoxane is the same as described above, and s represents the degree of polymerization, preferably 3 to 50.
  • the catalyst used in the present invention includes a catalyst containing the component (i) and the component (ii-1) as main components, a catalyst containing the component (i) and the component (ii-2) as main components, and the catalyst (i). ) Component, (ii-1) component, and (ii-2) component as main components.
  • the conditions for using the component (i) and the component (ii-1) are not limited, but the ratio (molar ratio) of the component (i): component (ii-1) is 1: It is preferably 0.01 to 1: 100, particularly 1: 1 to 1:10.
  • the operating temperature is preferably in the range of -100 to 250 ° C., and the pressure and time can be set arbitrarily.
  • the amount of the component (ii-2) used is usually 1 to 1000 mol, preferably 3 to 600 mol, per 1 mol of the component (i).
  • the activity can be improved by using the component (ii-2), but if the amount is too large, the organoaluminum compound is wasted.
  • the component (i) and the component (ii-1) may be contacted in advance to separate and wash the contact product before use, or the component (i) and the component (ii-1) may be contacted and used in the reaction system. Further, the component (ii-2) may be used in contact with the component (i), the component (ii-1) or the contact product of the component (i) and the component (ii-1). The contact may be made in advance or in the reaction system.
  • the dimerization reaction of the ⁇ -olefin is carried out in the coexistence of the ⁇ -olefin and the above catalyst in a hydrocarbon solvent, if necessary, at a temperature of 200 ° C. or lower, preferably 10 to 100 ° C. for 4 to 200 hours, preferably Can be carried out by stirring for 8 to 100 hours.
  • the reaction pressure is usually normal pressure or pressurized.
  • the dimer is deactivated with a compound having a hydroxyl group (for example, methanol), washed with an acid (for example, an aqueous hydrochloric acid solution or sulfuric acid) as necessary, and then the product (oil) is vacuum distilled.
  • Hydrocarbon solvents include aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, and simen, aliphatic hydrocarbons such as pentane, hexane, heptane, octane, decane, dodecane, hexadecane, and octadecane, cyclopentane, and cyclohexane. , Cyclooctane, methylcyclopentane and other alicyclic hydrocarbons, chloroform, dichloromethane and other halogenated hydrocarbons and the like. One of these solvents may be used alone, or two or more of these solvents may be used in combination.
  • ⁇ -olefin is an alkene having a carbon-carbon double bond at the ⁇ -position (terminal).
  • the ⁇ -olefins shown below can be used both in the production of the vinylidene olefin and in step 1 (step of obtaining an olefin oligomer) described later in the method for producing a saturated aliphatic hydrocarbon compound composition.
  • the ⁇ -olefin used for producing the vinylidene olefin is preferably an ⁇ -olefin having 6 to 12 carbon atoms, and more preferably an ⁇ -olefin having 8 to 10 carbon atoms.
  • n an integer of 7 to 15.
  • the linear ⁇ -olefin represented by is preferable, the linear ⁇ -olefin having 6 to 12 carbon atoms is more preferable, and the linear ⁇ -olefin having 8 to 10 carbon atoms is further preferable.
  • Specific examples of the ⁇ -olefin include 1-octene, 1-decene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene and the like.
  • ⁇ -Ocene, 1-decene, 1-dodecene and 1-tetradecene are preferable, and 1-octene and 1-decene are more preferable.
  • These ⁇ -olefins may be used alone or in combination of two or more.
  • the ⁇ -olefin used in step 1 (step of obtaining an olefin oligomer) described later in the method for producing a saturated aliphatic hydrocarbon compound composition is preferably an ⁇ -olefin having 6 to 12 carbon atoms, and 8 to 10 ⁇ -olefins. Oolefins are more preferred.
  • the general formula H 2 C CH- (CH 2 ) n- CH 3 (In the formula, n represents an integer of 7 to 15.)
  • the linear ⁇ -olefin represented by is preferable, the linear ⁇ -olefin having 6 to 12 carbon atoms is more preferable, and the linear ⁇ -olefin having 8 to 10 carbon atoms is further preferable.
  • ⁇ -olefin examples include 1-octene, 1-decene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene and the like. -Ocene, 1-decene, 1-dodecene and 1-tetradecene are preferable, and 1-octene and 1-decene are more preferable. These ⁇ -olefins may be used alone or in combination of two or more.
  • the method for producing a saturated aliphatic hydrocarbon compound composition of the present invention includes step 1 of oligomerizing the above-mentioned olefin to obtain an olefin oligomer.
  • This step is a step of oligomerizing the above olefin in the presence of a catalyst to obtain an olefin oligomer.
  • the catalyst used in this step is preferably an acid catalyst.
  • the acid catalyst include a Friedel-Crafts catalyst, a solid acid catalyst, a Lewis acid catalyst, and a Bronsted acid catalyst, and the Friedel-Crafts catalyst is more preferable. That is, step 1 is more preferably oligomerized in the presence of a Friedel-Crafts catalyst.
  • the Friedel-Crafts catalyst preferably contains an organoaluminum compound, more preferably an organoaluminum compound and an organic halide.
  • organoaluminum compound include trialkylaluminum, dialkylaluminum halide, alkylaluminum dihalide and the like, and dialkylaluminum halide is preferable.
  • organic aluminum compound include trimethylaluminum, triethylaluminum, triisobutylaluminum, diethylaluminum chloride, ethylaluminum sesquichloride, ethylaluminum dichloride and the like, and diethylaluminum chloride is preferable.
  • Examples of the organic halide include alkyl halides and allyl halides, and alkyl halides are preferable.
  • Specific examples of the alkyl halide include t-butyl chloride, sec-butyl chloride, cyclohexyl chloride, and 2,5-dimethyl-2-chlorohexane, and t-butyl chloride is preferable.
  • the molar ratio of the organoaluminum compound to the organic halide (organoaluminium compound / organic halide) when used in this step is preferably 1/10 to 1 / 0.5, more preferably 1/5 to 1/1. 1/4 to 1/2 is more preferable.
  • the ratio is 1/10 or more, the halogen content in the obtained oligomer can be reduced and removal becomes easy. Further, when the ratio is 1 / 0.5 or less, the reaction can be carried out with good reproducibility.
  • the concentration of the Friedel-Crafts catalyst used in this step is preferably 0.5 to 50 mmol / L, more preferably 0.6 to 20 mmol / L, as the molar amount of aluminum with respect to the volume of the substrate (olefin) at 25 ° C.
  • concentration of the catalyst is 0.5 mmol / L or more, the reaction can be carried out with good reproducibility, and when the concentration of the catalyst is 50 mmol / L or less, the halogen content in the obtained oligomer can be reduced. It can be removed easily.
  • the method for removing water and the like include a method in which an adsorbent is put into an olefin to adsorb and remove it, and a method in which an inert gas or a dry gas is bubbled and removed by an air flow, and it is preferable to use these in combination.
  • the adsorbent activated alumina and molecular sieve are preferable. Nitrogen is preferable as the bubbling gas.
  • the olefin used in this step is preferably a mixture of vinylidene olefin, ⁇ -olefin, vinylidene olefin and ⁇ -olefin described in the above-mentioned olefin, more preferably vinylidene olefin, and a mixture of vinylidene olefin and ⁇ -olefin. More preferred. Specific suitable olefins are as described above.
  • the dimerization reaction proceeds by bringing the catalyst and the olefin into contact with each other.
  • the reaction temperature during the dimerization reaction is preferably 0 to 100 ° C, more preferably 25 to 90 ° C, and even more preferably 30 to 80 ° C.
  • the reaction temperature is 0 ° C. or higher, the time until the reaction starts is short and the reproducibility of the reaction is good.
  • the reaction temperature is 100 ° C. or lower, the target oligomer can be obtained in a high yield without causing side reactions such as catalyst deactivation and olefin isomerization. Since this reaction is an exothermic reaction, the temperature rises during the reaction, but it is preferable to adjust the upper limit value to the above range.
  • the end point of the reaction can be determined by the elimination of heat generation.
  • the method for producing a saturated aliphatic hydrocarbon compound composition of the present invention includes step 2 of isomerizing the olefin oligomer obtained in step 1 (oligomerization step) to obtain an isomer.
  • This step is a step of isomerizing the olefin oligomer obtained in step 1 (oligomerization step) in the presence of a catalyst to obtain an isomer.
  • the olefin oligomer used in this step is obtained in the above step 1 (step of obtaining the olefin oligomer), and the reaction mixture may be used as it is or the catalyst may be removed, but the reaction mixture may be used as it is for the sake of production efficiency. It is preferable to use it.
  • the catalyst used in this step is preferably an acid catalyst.
  • the acid catalyst include a Friedel-Crafts catalyst, a solid acid catalyst, a Lewis acid catalyst, and a Bronsted acid catalyst, and the Friedel-Crafts catalyst is more preferable. That is, step 2 is more preferably isomerized in the presence of a Friedel-Crafts catalyst.
  • the Friedel-Crafts catalyst preferably contains an organoaluminum compound, more preferably an organoaluminum compound and an organic halide.
  • organoaluminum compound include trialkylaluminum, dialkylaluminum halide, alkylaluminum dihalide and the like, and dialkylaluminum halide is preferable.
  • organic aluminum compound include trimethylaluminum, triethylaluminum, triisobutylaluminum, diethylaluminum chloride, ethylaluminum sesquichloride, ethylaluminum dichloride and the like, and diethylaluminum chloride is preferable.
  • Examples of the organic halide include alkyl halides and allyl halides, and alkyl halides are preferable.
  • Specific examples of the alkyl halide include t-butyl chloride, sec-butyl chloride, cyclohexyl chloride, and 2,5-dimethyl-2-chlorohexane, and t-butyl chloride is preferable.
  • the molar ratio of the organoaluminum compound to the organic halide (organoaluminium compound / organic halide) when used in this step is preferably 1/10 to 1 / 0.5, more preferably 1/5 to 1/1. 1/4 to 1/2 is more preferable.
  • the ratio is 1/10 or more, the halogen content in each of the obtained isomers can be reduced, and removal becomes easy. Further, when the ratio is 1 / 0.5 or less, the reaction can be carried out with good reproducibility.
  • the concentration of the Friedel-Crafts catalyst used in this step is preferably 0.5 to 100 mmol / L, more preferably 1 to 40 mmol / L, as the molar amount of aluminum with respect to the volume of the substrate (oligomer) at 25 ° C. More preferably 1.5 to 20 mmol / L, even more preferably 2 to 10 mmol / L.
  • concentration of the catalyst is 0.5 mmol / L or more, the reaction can be carried out with good reproducibility, and when the concentration of the catalyst is 100 mmol / L or less, the halogen content in each obtained isomer is reduced. Can be and is easy to remove.
  • the concentration of the Friedel-Crafts catalyst specified here is the case where the Friedel-Crafts catalyst is used in the step 1 (step of obtaining the olefin oligomer) and the reaction mixture obtained in the step 1 is used as it is in the step 2. Is the concentration according to the total amount with the catalyst used in step 1.
  • the reaction temperature during the isomerization reaction is preferably 120 to 200 ° C, more preferably 130 to 190 ° C, and even more preferably 140 to 180 ° C.
  • the reaction temperature is 120 ° C. or higher, isomerization proceeds efficiently in a short time. Further, when the reaction temperature is 200 ° C. or lower, the desired isomer can be obtained in a high yield without causing a decomposition reaction.
  • the olefin oligomer obtained in the above step is isomerized by performing isomerization at a predetermined temperature using the catalyst, resulting in a more stable structure.
  • the details are not clear, but it can be considered as follows.
  • the main products of the olefin oligomer obtained in the above step using a 1-decene dimer are 13-methyl-11,13-dioctiltic lycosa-11-ene, 13-methyl-11,13-. It is considered to be dioctyl lycosa-10-ene and 11-methyl-11-octyl-13-octyldentricosan.
  • the reaction time during the isomerization reaction is preferably 1 to 240 minutes, more preferably 2 to 180 minutes, further preferably 3 to 160 minutes, still more preferably 5 to 140 minutes.
  • the reaction time is 240 minutes or less, the desired isomer can be obtained in a high yield without causing a side reaction such as a polymerization reaction.
  • the isomerization reaction is preferably completed by adding an alkali such as sodium hydroxide. After the reaction is completed, it is preferable to wash with water to remove the catalyst or salts derived from the catalyst.
  • the washing with water is preferably performed so that the mixture once made alkaline is neutral, and the pH of the water used for washing is preferably 9 or less.
  • the method for producing a saturated aliphatic hydrocarbon compound composition of the present invention includes a step 3 of hydrogenating the isomer obtained in the step 2 (isomerization step).
  • this hydrogenation step it is preferable to produce a saturated aliphatic hydrocarbon compound composition by vapor-phase hydrogenating the isomers using a hydrogenation catalyst.
  • a hydrogenation catalyst such as palladium or platinum
  • a nickel-based catalyst it is preferable to carry out the reaction at a reaction temperature of 150 to 250 ° C. and a hydrogen pressure of 1 to 20 MPa.
  • the amount of catalyst in each system is usually 0.05 to 50% by mass with respect to the isomer, and the hydrogenation reaction is completed in a reaction of 2 to 48 hours.
  • the hydrogenation reaction proceeds rapidly by using the above-mentioned hydrogenation catalyst, but even after the remarkable absorption of hydrogen has subsided, the remaining trace amount of unsaturated hydrocarbon compound is completely hydrogenated. , Additional operations such as heating or boosting may be performed.
  • Step 4 (distillation step)>
  • step 4 which is a distillation step after step 3 (hydrogenation step).
  • This distillation step is preferably carried out to remove impurities or hydrocarbon compounds having an undesired carbon number.
  • the distillation conditions may be appropriately changed depending on the number of carbon atoms of the target saturated aliphatic hydrocarbon compound composition and the like.
  • the saturated aliphatic hydrocarbon compound composition obtained by the production method of the present invention has a peak corresponding to the saturated aliphatic hydrocarbon compound (main component) having the highest carbon content in the chromatogram by gas chromatography.
  • the area of the main peak is preferably 40% or less, more preferably 35% or less, further preferably 30% or less, further preferably 25% or less, further preferably 23% or less, and more preferably 20% or less. More preferred.
  • the area of the peak in the chromatogram by gas chromatography can be determined by the method described in Examples, and the detector used here is a FID (hydrogen flame ionization detector).
  • the ratio of quaternary carbon per molecule is preferably 1.0% or less, more preferably 0.88% or less. 0.75% or less is further preferable, 0.63% or less is further preferable, 0.58% or less is further preferable, and 0.5% or less is further preferable.
  • the lubricating oil composition of the present invention contains the saturated aliphatic hydrocarbon compound composition described above. That is, the lubricating oil composition of the present invention is saturated with an evaporation loss of 4% by mass or less by the Noack method, an kinematic viscosity of 6.5 mm 2 / sec or less at 100 ° C., and an average carbon number of 36 to 44. Contains an aliphatic hydrocarbon compound composition.
  • the saturated aliphatic hydrocarbon compound composition is preferably 55% by mass or more, more preferably 60% by mass or more. When it is 55% by mass or more, the lubricating oil base oil does not volatilize, the weight loss is suppressed, and the number of oil changes can be reduced.
  • the lubricating oil composition of the present invention also includes a lubricating oil composition containing the saturated aliphatic hydrocarbon compound composition obtained by the above-mentioned production method. That is, the lubricating oil composition of the present invention includes a step 1 of oligomerizing an olefin to obtain an olefin oligomer, a step 2 of isomerizing the olefin oligomer to obtain an isomer, and a step 3 of hydrogenating the isomer. Contains the saturated aliphatic hydrocarbon compound composition obtained by the production method.
  • the saturated aliphatic hydrocarbon compound composition obtained by the above production method is preferably 55% by mass or more, more preferably 60% by mass or more.
  • the lubricating oil base oil does not volatilize, the weight loss is suppressed, and the number of oil changes can be reduced.
  • additives can be used in the lubricating oil composition of the present invention as long as the effects of the present invention are not impaired.
  • additives include antioxidants, oily agents, extreme pressure agents, cleaning dispersants, viscosity index improvers, rust inhibitors, metal inactivating agents, defoaming agents and the like.
  • an amine-based antioxidant As the antioxidant, an amine-based antioxidant, a phenol-based antioxidant, and a sulfur-based antioxidant used in conventional hydrocarbon-based synthetic lubricating oils can be used. These antioxidants may be used alone or in combination of two or more.
  • the blending amount of the antioxidant is usually about 0.01 to 10% by mass, preferably 0.03 to 5% by mass, based on the total amount of lubricating oil.
  • oily agent examples include fatty alcohols, fatty acid compounds such as fatty acids and fatty acid metal salts, ester compounds such as polyol esters, sorbitan esters and glycerides, and amine compounds such as aliphatic amines.
  • the blending amount of the oily agent is usually about 0.1 to 30% by mass, preferably 0.5 to 10% by mass, based on the total amount of lubricating oil, from the viewpoint of blending effect.
  • the extreme pressure agent examples include a sulfur-based extreme pressure agent, a phosphorus-based extreme pressure agent, an extreme pressure agent containing sulfur and a metal, and an extreme pressure agent containing phosphorus and a metal. These extreme pressure agents can be used alone or in combination of two or more.
  • the extreme pressure agent may be any one containing a sulfur atom and / or a phosphorus atom in the molecule and capable of exhibiting load resistance and wear resistance.
  • the blending amount of the extreme pressure agent is usually about 0.01 to 30% by mass, more preferably 0.01 to 10% by mass, based on the total amount of the lubricating oil composition, from the viewpoint of blending effect and economy.
  • cleaning dispersant examples include metal sulfonate, metal salicylate, metal finate, and succinate imide.
  • the blending amount of the cleaning dispersant is usually about 0.1 to 30% by mass, preferably 0.5 to 10% by mass, based on the total amount of the lubricating oil composition from the viewpoint of blending effect.
  • the viscosity index improver examples include polymethacrylate, dispersed polymethacrylate, olefin-based copolymer (for example, ethylene-propylene copolymer, etc.), dispersed-type olefin-based copolymer, and styrene-based copolymer (for example,). Styrene-diene hydride copolymer, etc.) and the like.
  • the blending amount of the viscosity index improver is usually about 0.5 to 35% by mass, preferably 1 to 15% by mass, based on the total amount of the lubricating oil composition.
  • rust preventive examples include metal-based sulfonates and succinic acid esters.
  • the blending amount of the rust preventive is usually about 0.01 to 10% by mass, preferably 0.05 to 5% by mass, based on the total amount of the lubricating oil composition from the viewpoint of the blending effect.
  • the metal inactivating agent examples include benzotriazole and thiadiazole. From the viewpoint of the compounding effect, the preferable compounding amount of the metal inactivating agent is usually about 0.01 to 10% by mass, preferably 0.01 to 1% by mass, based on the total amount of the lubricating oil composition.
  • defoaming agent examples include methyl silicone oil, fluorosilicone oil, polyacrylate and the like.
  • the blending amount of the defoaming agent is usually about 0.0005 to 0.01% by mass based on the total amount of the lubricating oil composition from the viewpoint of blending effect.
  • base oils can be used in combination with the lubricating oil composition of the present invention as long as the object of the present invention is not impaired.
  • other base oil mineral oil or synthetic oil can be appropriately selected.
  • the analysis method and evaluation method of the saturated aliphatic hydrocarbon compound composition obtained in each Example and Comparative Example are as follows.
  • Composition (distribution of carbon number) The composition of the saturated aliphatic hydrocarbon compound composition was measured using a gas chromatograph (Agient 6890N, manufactured by Agilent Technologies) using a solution of 0.1 g of a saturated aliphatic hydrocarbon compound composition in 25 mL of toluene under the following measurement conditions. ..
  • the components corresponding to each carbon number were calculated from the obtained chromatogram, and the composition (distribution of carbon number) was determined.
  • Injection temperature Oven track (column oven temperature + 3 ° C)
  • Detector temperature 430 ° C
  • FID Carrier gas He Linear speed: 40 cm / sec
  • Injection mode On-column injection Injection volume: 0.5 ⁇ L
  • Production Example 1 (Production of vinylidene olefin having 20 carbon atoms: Production of 1-decene dimer)
  • 1-decene dimer Production of 1-decene dimer
  • 1-decene dimer In a nitrogen-substituted three-necked flask with an internal volume of 5 liters, 4.0 L of 1-decene, 0.9 g (3 mmol) of bis (cyclopentadienyl) zirconium dichloride, which is a metallocene complex, and methylaluminoxane (WR Grasse)
  • a company-made product (8 mmol in terms of aluminum) was sequentially added, and the mixture was stirred at room temperature (20 ° C.). The reaction solution changed from yellow to reddish brown.
  • Example 1 (Production of Saturated Aliphatic Hydrocarbon Compound Composition (1)) (1) Oligomerization step (step 1) Activated alumina (NKHO-24, manufactured by Sumitomo Chemical Co., Ltd.) is added to the C20 olefin (1) obtained in Production Example 1, and bubbling treatment is performed with nitrogen in order to remove water and the like, and a drying treatment C20 olefin (dry treatment C20 olefin (1)) is performed. 1) was obtained.
  • Activated alumina Activated alumina (NKHO-24, manufactured by Sumitomo Chemical Co., Ltd.) is added to the C20 olefin (1) obtained in Production Example 1, and bubbling treatment is performed with nitrogen in order to remove water and the like, and a drying treatment C20 olefin (dry treatment C20 olefin (1)) is performed. 1) was obtained.
  • a three-necked flask equipped with a three-way cock, a thermometer, and a stirrer is replaced with nitrogen, and 1968 mL of the dried C20 olefin (1) is added and heated in an oil bath while stirring to raise the temperature of the dried C20 olefin (1).
  • the temperature was set to 30 ° C.
  • 6.0 mmol of tert-butyl chloride and 2.0 mmol of diethyl aluminum chloride (DEAC) were added as catalysts.
  • tert-butyl chloride and diethylaluminum chloride (DEAC) a solution diluted with the drying-treated C20 olefin (1) to 0.5 mol / L was prepared in advance, and these solutions were added.
  • the temperature of the reaction solution rose 10 minutes after the addition of the catalyst, and stopped 2 minutes after that. From this, it can be seen that the oligomerization is completed.
  • step 2 the temperature of the reaction solution was adjusted to 150 ° C., and 6.0 mmol of tert-butyl chloride and 2.0 mmol of diethyl aluminum chloride (DEAC) were added thereto as catalysts. The addition method is the same as the previous step. After reacting at 150 ° C. for 1 hour, the reaction solution was cooled to 60 ° C., 160 mL of 1.0 mol / L sodium hydroxide aqueous solution was added, and the mixture was stirred to remove the sodium hydroxide aqueous solution.
  • DEC diethyl aluminum chloride
  • the saturated aliphatic hydrocarbon compound composition obtained in Example 1 has a loss on evaporation of 4% by mass or less by the Noack method and a kinematic viscosity at 100 ° C. of 6.5 mm 2 / sec or less.
  • the obtained lubricating oil has a long life.
  • Production Example 2 (Production of a mixture of vinylidene olefin having 20 carbon atoms and ⁇ -olefin having 10 carbon atoms: a mixture of a dimer of 1-decene and 1-decene)
  • 1000 L of 1-decene was added to a heat-dried reactor having an internal volume of 1500 L, 1.33 L of 3 mol / L methylaluminoxane was added, and the temperature was raised to 35 ° C.
  • Example 2 (Production of Saturated Aliphatic Hydrocarbon Compound Composition (4))
  • the saturated aliphatic hydrocarbon compound composition (1) of Example 1 instead of the C20 olefin (1) obtained in Production Example 1 used in the (1) oligomerization step (step 1), Production Example Using the C20 / C10 olefin (2) obtained in No. 2, the same procedure as in Example 1 except that the distillation conditions in the (4) distillation step were set to conditions suitable for the present saturated aliphatic hydrocarbon compound composition.
  • a saturated aliphatic hydrocarbon compound composition (4) was obtained.
  • the ratio of the main peak area to the 40 carbon components by gas chromatograph analysis was 16%.
  • the composition and characteristics of the obtained composition are shown in Table 2.
  • Comparative Example 3 (Production of Saturated Aliphatic Hydrocarbon Compound Composition (5)) Saturated fat having an average carbon number of 40 in the same manner as in Example 2 except that (2) the isomerization step (step 2) was not performed in the production of the saturated aliphatic hydrocarbon compound composition (4) of Example 2. A group hydrocarbon compound composition (5) was obtained. The ratio of the main peak area to the 40 carbon components by gas chromatograph analysis was 80%. The composition and characteristics of the obtained composition are shown in Table 2.
  • the production methods of Examples 1 and 2 can obtain a saturated aliphatic hydrocarbon compound composition having a small evaporation loss even though the kinematic viscosity is low as compared with the production methods of Comparative Examples having the same average carbon number. Is clear. From this, the saturated aliphatic hydrocarbon compound composition obtained in the examples is an excellent lubricating oil base oil that does not deteriorate for a long time even when used as a lubricating oil for machines that needs to have a low viscosity. It can be seen that it is.
  • Production Example 3 (Production of a vinylidene olefin mixture having 16 to 24 carbon atoms: Production of a dimer of a mixture of 1-octene, 1-decene and 1-dodecene) Put 666 mL each of 1-octene, 1-decene and 1-dodecene in a glass container with an internal volume of 2 L that has been heat-dried and replaced with nitrogen, and a toluene solution of methylaluminoxane (20 mmol in terms of aluminum) and a hexane solution of diethylaluminum chloride.
  • Example 3 (Production of Saturated Aliphatic Hydrocarbon Compound Composition (6))
  • the saturated aliphatic hydrocarbon compound composition (1) of Example 1 instead of the C20 olefin (1) obtained in Production Example 1 used in the (1) oligomerization step (step 1), Production Example Using the C16 to 24 olefin (3) obtained in step 3, ethyl aluminum sesquichloride (EASC) was used in place of diethyl aluminum chloride (DEAC) in (step 1) and (step 2), and (4) distillation was performed.
  • EASC ethyl aluminum sesquichloride
  • DEAC diethyl aluminum chloride
  • a saturated aliphatic hydrocarbon compound composition (6) having 32 to 48 carbon atoms as a main component was obtained in the same manner as in Example 1 except that a distillate of 196 ° C./24.0 Pa or less was removed in the step. It was.
  • the composition of the obtained composition and each property are shown in Table 3.
  • Comparative Example 4 (Production of Saturated Aliphatic Hydrocarbon Compound Composition (7))
  • the carbon number of the main component is the same as that of Example 3 except that (2) the isomerization step (step 2) was not performed.
  • a saturated aliphatic hydrocarbon compound composition (7) of 32 to 48 was obtained.
  • the composition of the obtained composition and each property are shown in Table 3.
  • the production method of Example 3 obtains a saturated aliphatic hydrocarbon compound composition having an extremely small evaporation loss while maintaining the kinematic viscosity substantially the same as that of the production method of Comparative Example 4 having the same average carbon number. It is clear that can be done. From this, the saturated aliphatic hydrocarbon compound composition obtained in the examples is an excellent lubricating oil base oil that does not deteriorate for a long time even when used as a lubricating oil adjusted to a specific viscosity. Recognize.

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Abstract

L'invention concerne une composition de composé hydrocarbure aliphatique saturé qui présente une perte par évaporation inférieure ou égale à 4% en masse selon le procédé de Noack, une viscosité cinématique à 100°C inférieure ou égale à ６,５ｍｍ2/seconde, et un nombre moyen de carbone compris entre ３６ et ４４. L'invention concerne également une composition d'huile lubrifiante comprenant cette composition de composé hydrocarbure aliphatique saturé. Enfin, l'invention concerne un procédé de fabrication de composition de composé hydrocarbure aliphatique saturé qui inclut : une étape (1) au cours de laquelle une oléfine est soumise à une oligomérisation, une étape (2) au cours de laquelle un isomère est obtenu par isomérisation de cet oligomère d'oléfine, et une étape (3) au cours de laquelle cet isomère est hydrogéné.
PCT/JP2020/028118 2019-07-25 2020-07-20 Composition de composé hydrocarbure aliphatique saturé ainsi que procédé de fabrication de celle-ci, et composition d'huile lubrifiante WO2021015172A1 (fr)

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MX2022000890A MX2022000890A (es) 2019-07-25 2020-07-20 Composicion de compuesto de hidrocarburo alifatico saturado, composicion lubricante y metodo para producir la composicion de compuesto de hidrocarburo alifatico saturado.
CN202080052938.1A CN114127238B (zh) 2019-07-25 2020-07-20 饱和脂肪族烃化合物组合物、润滑油组合物、以及饱和脂肪族烃化合物组合物的制造方法
JP2021534030A JP7525491B2 (ja) 2019-07-25 2020-07-20 飽和脂肪族炭化水素化合物組成物、潤滑油組成物及び飽和脂肪族炭化水素化合物組成物の製造方法
EP20844170.9A EP4006126A4 (fr) 2019-07-25 2020-07-20 Composition de composé hydrocarbure aliphatique saturé ainsi que procédé de fabrication de celle-ci, et composition d'huile lubrifiante
CA3148235A CA3148235A1 (fr) 2019-07-25 2020-07-20 Composition de compose hydrocarbure aliphatique sature ainsi que procede de fabrication de celle-ci, et composition d'huile lubrifiante
KR1020227005498A KR20220042152A (ko) 2019-07-25 2020-07-20 포화 지방족 탄화수소 화합물 조성물, 윤활유 조성물 및 포화 지방족 탄화수소 화합물 조성물의 제조 방법
US17/629,173 US20220251461A1 (en) 2019-07-25 2020-07-20 Saturated aliphatic hydrocarbon compound composition, lubricant composition, and method for producing saturated aliphatic hydrocarbon compound composition

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